The strongest nitrogen base is 1,8-bis(dimethylamino)naphthalene-2,7-diolate according to experimental data and DFT calculations. Its proton affinity (PA) is comparable to those of simple ions such as OH−, NH2−, and H−. The diaminonaphthalene diolate 2 is protonated at the neutral amino groups with extremely high gas-phase and solution proton affinity to form highly stable H-bonded conjugate acid 1. DMSO=dimethyl sulfoxide.
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Ozeryanskii et al. (2006) studied this question.
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